S-[(1S)-3-oxocycloheptyl] benzenecarbothioate | 1370607-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: S-[(1S)-3-oxocycloheptyl] benzenecarbothioate
• CAS: 1370607-99-0
• 化学式: C₁₄H₁₆O₂S
• 分子量: 248.346
• InChiKey: ZTBHVNMQWMYZFJ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  59.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫代苯甲酸 、 2-环庚烯-1-酮 在 N-[3,5-双（三氟甲基）苯基]-N''-[（8α，9S）-6''-甲氧基七氢呋喃-9-基]脲 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 、 S-[(1S)-3-oxocycloheptyl] benzenecarbothioate
  参考文献：
  名称：

  Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst

  摘要：

  Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2012.02.052

文献信息

• Enantioselective sulfa-Michael addition of thioacids to α,β-unsaturated ketones with bifunctional organocatalyst
  作者：Nirmal K. Rana、Rajshekhar Unhale、Vinod K. Singh

  DOI：10.1016/j.tetlet.2012.02.052

  日期：2012.4

  Organocatalytic conjugate addition of thioacids to alpha,beta-unsaturated ketones has been studied in the presence of cinchona alkaloid derived urea catalyst. Both the enantiomers of products are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The catalytic process provides optically active thioesters with high chemical yields (up to 99%) and useful enantiselectivity (up to 83% ee). The reaction was performed with 1 mol % of catalyst in toluene at room temperature. A transition state model has been proposed to explain the stereochemical outcome of the reaction. (C) 2012 Published by Elsevier Ltd.